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14 People Share Their Most Awkward Attempts At Flirting

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I don’t flirt because I suck at it.

You’re about to meet 14 people who flirted and failed miserably.

After reading many of these, I feel very good about my decision to not flirt.

14. SQUIRT!!!

I went to Israel on birthright. towards the beginning of the trip, we had a 5 hour bus ride through the desert. I was pretty sleep deprived already and somehow managed to get the best looking girl on the trip to sit with me for the ride. After an hour or so of chatting it up, I decided to take it to the next level, and put my arm around her. Surprisingly, she was into it. We both fell asleep like this for around 20 mins.

We then woke up and she went to take a drink from her 1 liter water bottle. I decide for some completely unknown reason that it would be funny and flirty to squeeze the hell out of the bottle. It explodes all over her face and clothes drenching her. I was almost as surprised as she was.

I instantly apologized for my “joke” and we rode for endless hours through the desert in moist awkward silence and I blew my chances obviously.

TL:DR- Had a long bus ride with a hot girl, squirted all over her face, she was not pleased.

13. What’s The Rub?

Oh man. This one burns to relive. About a year and a half ago, I flew into Montana and drove straight to Jackson Hole, Wyoming, with a good buddy of mine. We started drinking pretty heavily at the rodeo, and decided to eventually saddle up at the Million Dollar Cowboy bar.

When we walked in, there was space at the back bar, so we took our positions. Within minutes, we were surrounded by 20 girls from a bachelorette party. Money.

Pause for relevant context: * I had been up for about 20 hours off of 3 hours of sleep * I don’t have cash, and this is an all cash bar * My buddy, now sitting on my left, is very smooth with girls, and I was in the middle of a dry spell

One of the girls comes up and sits down on my right, chatting me up. She’s gorgeous, and I’m pumped.

After a few minutes, my buddy starts rubbing my leg. I’m a little confused, but figured he was giving me a “hint”, and start mirroring his behavior by rubbing the girl’s leg. After a few more minutes, he starts rubbing more vigorously. I’m thinking to myself, “this actually works?”, but nevertheless start rubbing her leg more vigorously.

The conversation quickly deteriorates, and she runs off in a hurry to join her friends on the dance floor. I turn to my buddy and he says, “take the f-ing 20!”, “What 20?”, “The $20 I’m rubbing on your leg so you can buy her a drink!”

She came back 5 minutes later wearing a wedding ring. I’m positive she wasn’t married, just applying some douche repellent.

12. Pure Fire

In high school, when I was 14 or 15, I rode the bus with a girl who had blossomed early. She was from a different group from me and we did some occasional flirting but chances for actual interaction were rare.

While we were standing around waiting for the busses to arrive one day, I noticed that she was wearing jeans shorts cut very short on top of her very long legs. For some reason, I thought it would be hilarious to light the fringe of her jeans shorts on fire with my lighter (keep in mind…I was guided only by hormones). I thought it would be like a sockfire or something. Like “woosh!” and then out.

So when her back was turned I lit the lighter right under her butt, and of course immediately the frayed cotton of the shorts went right up and showed no indication of going right out. Immediately I recognized that I had made a major error and I commenced slapping at her upper thigh/ass area in an attempt to get it out.

It did go out, but of course I had run up behind her and apparently begun roughly grabbing at her ass, from her perspective. Attempting to smooth it over with “I was trying to put out the fire that I had set upon you” didn’t go over any better, and needless to say I could have gone to jail.

She just decided to avoid me (and rightly so) from then on out.

TL;DR – I set a girl I liked on fire.

11. You Too?!

After encouragement, a drunk friend of mine wandered over to a hot chick at a loud party and stumbled into the following exchange:

“Hey! My name’s Luis! What’s your name?”

“Luis??” struggling to hear

“Haha! Oh wow! Your name’s Luis too! That’s so crazy!”

[…]

“…I’m really drunk.” wanders off

10. Not That Innocent

I was pretty innocent at 16 and was flirting with a guy on my swim team.

For some reason he was wagging his finger in my face, so I snatched it and moved it towards my face…I dunno, I think I was pretending to bite it, just being feisty.

He had this intense look on his face, and as I moved the finger to my mouth I suddenly realized, horrified, what it actually looked like.

I dropped his hand and ran out of the room- we didn’t talk for months, I was so embarrassed I didn’t even want to see him.

9. Bathroom Behavior

I was once smitten with a bartender and thought it would be cute to leave him a paper boat made of toilet paper in the bathroom.

Upon my return, I said in my sexiest voice… “I left you something in the bathroom”.

I wanted to slap my forehead as soon as that sentence escaped my mouth.

8. Wait…. What?!?

My buddy once sat nervously at a bar waiting to talk to a very attractive girl.

He finally got up the courage to go talk to her but when he got close to her, he instead punched her in the back and ran away.

It remains the saddest male-female interaction I’ve ever seen.

7. Transformed Into A Trash Panda

I was playing frisbee with a group of people. I threw it at this really cute girl.

Who, I swear, was looking at me when i threw it… she turned around as it was still in flight. Someone called her name and she turned just in time to have this frisbee hit right between the eyes.

Nearly knocked her out. Definitely knocked to the ground.

I spent the next 2 hours apologizing. She got a beautiful set of raccoon eyes from that hit.

Bam!

6. POKE!

While on a ride in Disney world back in middle school, I turned to the girl sitting beside me (a classmate) that I had been joking with most of the ride and put my hands up making “woo” ghost noises. It was the dark part of that “it’s a small world after all” ride.

Anyway, I poked her in the eye and knocked out her contact.

She had to go back to the hotel to get her glasses.

5. One time…

One time, I gave a girl some zip ties.

Another time, I fixed a girl’s vacuum cleaner.

Another time, I touched the legs of every girl at a party.

Another time, I was talking to a girl who snorted when laughing and made a reference to this fact in an attempt to tease her, but it was completely out of context and thus awkward.

Another time, in 8th grade, I remembered a girl’s phone number and address from the school directory, and then shared this fact with her.

Another time, I had a prolonged e-mail exchange with a girl about some national instruments D/A boards that neither of us were particularly interested in.

I did not get any those times, or any other time.

4. Yeah, don’t be that guy.

The prettiest girl I ever knew was into me.

She moved away for college and me and my friends planned a trip to the city she was staying in and I told her we could meet up at some point. It was the afternoon, and we weren’t going to meet up until that night, so my friends and I went to a park and started to drink a few beers.

A few beers turned into a bottle of whiskey and then some guy sold us a bunch of ecstasy. By the time we got to her house I was real messed up. I knew I was acting weird too, and I tried to stop, but I think that made me act more weird.

I ended up passing out on her couch and I woke up at 3 in the morning covered in my piss.

I snuck out and took a taxi back to the place I was staying at.

We used to talk a lot, but we don’t anymore.

3. Absolutely Scarring

Hanging with a friend and a few girls in a park. The topic turns to how manly me and my friend are. I said that I can take any kind of pain and not even flinch. The one girls calls me on it and starts flicking my ear, pinching me, etc.

After about 10 things she says I bet I can burn you with my cigarette and it will hurt. I say go for it so she puts her cigarette out on my arm. It hurt like hell but she was cute so I never flinched. She was impressed so we talked a bit more by ourselves at a picnic table.

We are getting ready to go and I stand up, smack my knee on the table and the whole table collapses. She looked at me and says “Well, you had me up until that.”

2. Chipmunk Cheeks

There was a super cute girl in some humanities class I had a year or two ago (I go to an engineering school so not only do I not normally take humanities classes, there are also not normally super cute girls), and the most that would happen between was that we would smile politely at each other upon one or the other entering the room.

One day I was going towards class with a slice of pizza in my hand, eating as I went. I passed her going the other way and she waved and said “Hi!”

I waved back and answered “PFFFGH!” This was because of the mouthful of pizza I was sporting, chipmunk-getting-ready-to-hibernate style.

Some crust fell out too, just to make completely certain I would never speak to her again.

1. Glitter Bomb

This story begins three years ago. It was an ordinary day and I needed to use an ATM. I stopped by the Publix and used one of the outdoor ATMs. On my way back to my car, I noticed something glistening in the hot, bright, summer sun. It was a small, partially opened bag of glitter. There’s a Michael’s in this shopping center so a valid assumption would be that it came from there and via happenstance some poor soul dropped the baggie on the ground.

Naturally, I did what any normal human being in my situation would do. I pocketed the hell out of that glitter. You never know when you’ll need glitter.

With the glitter in my pocket I proceeded along with my day. What followed was a typical day, that is, until I wanted to buy myself a book. I made my way to Barnes and Noble. I perused the books when out of the corner of my eye I saw a cute girl. She was so adorable and she also happened to work there.

I have this rule: Don’t hit on women while they’re working. Just don’t bother people with personal stuff while they’re working because you’re not special and every other mundane schmoe out there thinks he’s special when he flirts with the cute waitress. So I hit on her.

I asked for her help and made with the joking banter. She was digging it and inevitably asked me for my name. I said “Orlando…” and I followed it up with what I consider the stupidest flirting move anyone has ever pulled ever. I reached into my pocket and pulled out a handful of glitter. I perfectly synchronized throwing this handful into the air with the next words that left my mouth:

“Like Orlando Magic.”

GLITTER EVERYWHERE. Why did I do this? I thought it would be so stupid it would make her laugh, and perhaps entice her to bed me. I pride myself (or, I used to) in pushing the envelope when it comes to courting. This, I learned about a second after the magical thrust of pixie dust, was not one of those situations.

Like I said, glitter everywhere. Mostly her face.

“OWWWW MY EYE, MY EYE, MY EYE!!”

Glitter to the face. Was I a gentleman? No. I walked out. Not just walked out, speed walked. I acted completely oblivious to this girl and the fact that I just maced her with sparkling iridescent plastic bits.

I went back to the store years later. I had, for the most part, forgotten all about what happened here for a brief moment until I entered. Then I had this “oh, right, I’m an ass” moment. I didn’t turn around and leave because I assumed after 3 years this girl wouldn’t still be working here. I was right.But… she just happened to be shopping here. And not only was she there, but she wasted no time in walking toward me. I wanted to bless her with a little déjà vu and speed walk out of there, but I couldn’t. I was so shocked by the fact that this was happening that I couldn’t even move. When she finally arrived and stood right in front of me, I felt defeated and emasculated. We’re face-to-face. and she says, “hey Glitter, WTF?”

She didn’t seem mad. She just had this slight look of disapproval, and I frankly expected her to kick me in the balls at the very least. I wasn’t sure how to respond so I defaulted into snarky-Orlando-mode.

I looked at her plainly and just said: “…did you at least get the joke?”

She just busted out laughing and then walked away.

Crazy.